Friends and Lovers
by LightLeadingMe
Summary: Jack and Karen form some sort of 'friends with benefits' relationship. How Will their friends react?
1. Pt 1

Jack let out a loud groan, his hands gripping at the shoulders in front of him. He tossed his head back slightly, letting the pleasure consume him as he felt sharp nails dig into his buttocks. He felt the urge to thrust his hips, but knew he would get yelled at if he dared move, so he kept his ground, biting his lip to suppress any movement. He gasped and then shuddered when he felt the tongue wrapped around his shaft move down to his balls, the mouth suckling as the hand pumped leisurely.

"Ahh, oh my- I'm gonna cum," he breathed out, feeling his orgasm rise within him.

"Don't you dare," a voice said below him, muffled by his flesh.

He squeezed his eyes shut, trying to hold off. "P-please let me cum!"

"Look at me."

He forced his eyes open and looked down just in time to watch Karen's mouth take him all the way in, sucking hard while she bobbed her head back and forth at a steady pace. They locked their eyes on each other and Jack tangled his fingers in her brown locks, his body going stiff as he finally came, shooting jets down her throat. Karen swallowed it all, moaning in appreciation. She pulled back, letting him go with a 'pop' and then took him in again, licking him slowly until he softened in her mouth.

He didn't push her away from his sensitive cock, knowing she would punish him if he did. She would move away when she was ready to and he honestly didn't mind the torture, teetering on the boarder of pleasure and pain. He watched her adoringly, his fingers stroking through her hair as she stroke him with her tongue. With a final moan, she pulled away, placing a delicate kiss to the head before she tucked him back into his boxers and zipped up his pants. He helped her up from her knees and leaned down to accept her kiss.

"Mmm, I love your cock, Jackie," she moaned into his mouth. Her tongue sought his out and they made out for a few minutes. Karen was the one to pull away, giving him a little wink before she walked away towards his bathroom to fix her makeup.

When Jack heard the click of the lock sliding into place, he leaned heavily against the front door of his apartment, swiping a hand across his face as he took in deep breaths. This all started months ago. One night Jack had asked if she was any good at blow jobs. Instead of telling him how good she was, she decided to show him instead. And now, months later, they couldn't get enough of each other.

But Jack was beginning to feel bad. Karen always got him off, doing wicked things to his cock, but she knew he was uncomfortable when it came to a woman's body so she would scamper off to a different room to take care of herself. She deserved more. He realized more recently that he couldn't be that replused by a women's body if he was easily getting off with Karen. His favorite thing she did to him was when she gave him a titty fuck. He loved her tits, loved to play with them, but he especially loved when his cock was between them, her mouth wrapped around the head.

One time, when she was finished with him and excused herself to the bathroom, he followed her, pressing his ear to the door, listening to her high pitched moans. Curiosity got the best of him and he turned the knob, peeking inside. He saw her sitting upon the sink with her hand under her skirt, her panties shoved in her mouth to stifle the loud sounds of pleasure escaping her. Her eyes were closed and her eyebrows knit together as she concentrated on finding her release. Jack felt a stir in his pants and quickly, but quietly shut the door, surprised at his body's reaction. He had suddenly felt the urge to go to her. He wanted to be the one to bring her that pleasure. He wanted to know what she looked, felt, and sounded like when she came.

Hearing the bathroom door open, Jack snapped from his thoughts and watched as Karen emerged from the bathroom, her makeup flawless and hair back in place. She gave Jack a devious grin as she stepped up the kitchen steps to grab herself a drink. Jack quickly followed, hovering over her as she made a martini. He was nervous, not exactly sure where to put his hands or what to say.

"K-Kare?" he asked tentatively.

"Yeah, honey?"

He licked his lips, his nerves getting the best of him. "You know how you're always taking care of me and then you run off to... take... take care of yourself because you don't want to make me uncomfortable?"

Karen stopped making her drink and slowly set the martini shaker on the counter, looking over her shoulder at him. "What are you saying, Jack?"

Jack gulped, mustering up the courage to finish what he started to say. "I don't want you to run off anymore," he blurted out. Karen turned to face him in shock. He continued before she could speak up. "I want to help you like you help me. I want to know what you taste like. I want to watch you when you cum... "

Karen just stared at him, her jaw dropped. She licked her lips and shook her head, trying to wrap her brain around the concept. "So you wanna... fuck me?"

"Oh God no!" He exclaimed, placing his hands on her shoulders. "No. I love you, but I don't think I could ever have sex with a woman." She deflated, but he wasn't sure if it was from relief or disappointment. "But I do want to pay you back."

"Jackie," she smiled. "You don't have to-"

"I don't," he agreed, cutting her off. "I want to."

Minutes later, he had her naked and on all fours on his bed. Her ass was red with his handprints. He knew Karen liked it rough from the many stories she told him of her sexual trysts and be wanted to make this experience just as pleasurable for her. She was gripping the sheets, her pussy dripping with arousal. Jack, sitting on his knees behind her, tapped her thighs, telling her to spread her legs further apart. She complied and he smirked, placing his fingers at her entrance.

Karen whimpered and gasped as he teased her, his fingers tracing her lips, but never going to where she needed them most. "Jack, please," she begged, her chest heaving with deep breaths.

Jack smirked and relented, pressing two fingers against her swollen clit. She shuddered and moaned as he drew circles into her. He continued to tease her for a bit, bringing her to the edge and then slowing down. She was getting more and more frustrated with each passing second. Just as she was about to snap at him, Jack slipped two fingers into her and twisted them down, pumping them wildly into her. Karen cried out, the pleasure consuming her. She arched her back up and began to squeeze her knees together as she felt the orgasm tingle up her body until it finally erupted and she screamed. She contracted around him, squeezing his fingers tight.

"Come on, Karen," Jack said with a sly grin. "You can do better than that." He added a third finger and moved his hand even faster than before, applying pressure to her G-spot.

Karen was still trying to catch her breath from her first orgasm when her second ripped through her twice as intense. "Ohhh my gaahh- JACK!" She sobbed, her muscles contracting and pulsating.

Jack grinned triumphantly when she began to squirt, coating his arm and the sheets. "There you go," he said. He pulled his fingers out and smacked her clit a few times causing her to squirt a little more. Karen fell to her side on the bed, trembling as little jolts of pleasure continued to shoot through her body. Jack crawled up next to her and rubbed her back soothingly. "You okay?"

She nodded, taking in deep breaths. "Fuck," she gasped, glancing up at him. "That was incredible."

"Yeah?" he smiled shyly down at her. "Was I that good?"

"Oh honey, I saw stars. And I don't mean figuratively. I was fucking _flying_."

Jack let out a laugh and settled himself down under the covers next to her, pulling them up over their shoulders. Karen scooted herself back against him and sighed in content. "So now every time you do something for me, I'll do it right back."

Karen looked back over her shoulder at him again. "You know I told you that you don't have to."

"And I told you that I want to, Karen," he said with a shake of his head. "You're my best friend. We know everything there is to know about each other."

"So," she frowned and turned over in his arms on her back so she could look up at him. "What are we, friends with benefits?"

Jack contemplated the phrase for a moment. "Yeah, I guess we are."

"Well good," she grinned and reached up to peck his lips.


	2. Pt 2

Jack woke up to light clanking sounds coming from the kitchen. He frowned, his mind slightly foggy from the night previous, until he heard a high pitched curse and then he smiled as memories flooded his mind. He and Karen didn't fall asleep until almost 4 am, their sexual antics keeping them awake most of the night. It had been almost six months since they started their "friends with benefits relationship" and they still couldn't get enough of each other. They still dated on the side, but they kept finding themselves running to each other the second the relationship didn't work out, which was becoming more and more frequent.

He heard another crash and a louder curse this time and he decided to get up from the bed to make sure Karen wasn't single handedly destroying his kitchen. He pulled on his boxers that were haphazardly tossed by the door and exited the bedroom to find Karen mixing together her breakfast - a bloody mary. He observed her for a moment from the doorway. She had slipped a nightgown on, one that she kept in one of his drawers. It was light pink in color and short, barely covering her ass. Every time she bent over he could see just the bottom of her cheeks. He bit back a giggle when Karen grumbled under her breath again, seeming to be fighting a losing battle with the blender.

Quietly, Jack crept up behind her, knowing the perfect way to relieve her frustration. He slid his arms around her waist from behind, his hand settling on her stomach. Karen jumped, startled.

"Oh, honey," she gasped, placing on hand over his, the other still grasping the blender. "You scared me."

"Sorry," he murmured, his voice muffled by the skin of her neck while he trailed his lips down to her shoulder.

Karen returned to her task of making her drink and Jack kept kissing her neck, his teeth biting gently and his lips sucking. His hands moved up her stomach to her breasts where he pinched and squeezed, earning a moan from Karen who seemed to have forgotten about what she was doing. In a flash, Jack grabbed Karen by her hips and spun her around. Their lips connected instantaneously and Jack lifted her up onto the counter, pushing the ingredients off to the side. Karen had her legs wrapped around his waist, her nails scratching at his bare back. Jack moved his hands up her thighs, pushing her nightgown up until it was bunched around her waist. He moved a hand between her legs and groaned when he realized she wasn't wearing any panties and that she was already dripping wet. He slid two fingers into her and moved them back and forth slowly. Karen groaned against his mouth, biting his lip in frustration.

"Harder," she pleaded, pulling her mouth from his to stare into his eyes.

Jack stepped from between her legs and moved to the side of her, his arm coming around her back to rest on her hip to keep her steady. Karen turned her head and he latched his mouth to hers just has he added a third finger, his hand now pumping almost recklessly. Karen cried out as the sensation hit her and placed her hands on either side of her on the counter, her knuckles turning white as she gripped the edge beneath her fingers. She rolled her head to the side and her eyes rolled back into her head as her orgasm began to sweep over her body. She began to squeal out higher and higher in pitch, finally yelling her release when the door to Jack's apartment flung open.

"Hey, Jack, I was- Oh my God!" Will screamed.

Jack quickly withdrew his hand from between Karen's legs and let out a shocked cry. "Will, what are you doing here?" he shrieked.

Karen, coming down way too fast from her orgasm, covered herself up and slid off the counter top onto wobbly legs. She looked between a horrified Will and a semi-aroused, yet very displeased Jack.

"What the hell are you doing?" Will asked, ignoring Jack's question as he pointed between the two of them.

Karen rolled her eyes and stepped down from the kitchen, grimacing as her cum ran down her thighs. "He was finger banging me, Wilma. Duh." She looked over her shoulder at Jack calmly. "I'm gonna take a shower, honey."

With that, she disappeared into the bathroom, leaving Will and Jack to stare at each other. Jack, finally able to get his erection under control, walked around the counter and down from the kitchen to face Will.

"Are you having sex with a woman?!" Will asked, ripping the band-aid right off.

"What?!" Jack exclaimed, a hand to his chest in shock. "No!"

"Then what the hell do you call that?!" Will shouted back, his hands wildly gesturing to the kitchen and the acts that just transpired there.

"Karen already told you," Jack sighed in annoyance, crossing his arms over his chest.

"So, what, you were actually fingering a woman?"

"No, I was fingering Karen."

"Karen _is_ a woman, Jack!"

It was silent after that. The two friends just stared at each other, both now confused. The shower turned off in the distance and Karen emerged from the bathroom, a poof of steam following her.

"Oh, you're still here," she commented, holding her towel tighter around her chest.

" _Yes_ ," Will growled. "I'm still here. And _I'm_ still queer!"

"What's that supposed to mean?" Jack scoffed, his face scrunched up.

Will ignored him, his eyes now darting back and forth between him and Karen. "How long has this been going on?"

Karen shrugged, looking bored. "About six months."

" _Six months_!"

"Will," Jack prompted his friend. "What did you mean you're still queer. I'm gay, too."

"Jack," Will put his hands on his hips, a sympathetic and condescending look covering his features. "You've been sleeping with Karen..."

"Technically, we haven't had full on sex," Karen piped up, squinting her eyes together. "We have a slight agreement." She smiled fondly at Jack and he grinned back, almost shy. "Whenever one of us needs to get our hose drained or our bush whacked, we hop into bed with each other and get to gettin' off. Or on the couch... or the shower-"

"I get it," Will held his hand up, his eyes closed, trying to erase any images Karen just brought forth to his mind. "What I don't get is how this happened?"

"Well, I asked Karen if she was good at blow jobs, she showed me she is and from then on we kinda just started our shenanigans. Like a booty call!"

Karen jumped up and down, clapping her hands together as Jack giggled with her. Will just stared on incredulously. "So, what, you're bi now?"

"Bite your tongue!" Jack pointed his finger accusingly at him. "I'm as gay as the day is long!"

"But you have a sexual relationship with Karen!"

"Oh for Godsakes, Wilma," Karen sighed in exasperation. "Sex is sex! We're still dating other people! It's just when things don't work out or we just need a quick release so to speak we come to each other. Haha," she giggled. "Cum."

Jack snickered beside her, poking her playfully while she slapped his hands away.

"This is ridiculous," Will said, throwing his hands in the air. He rushed to the door and turned to face them again. "I don't know what this is, I just know it's... it's _wrong_." He left the apartment, going across the hall and slamming the door behind him.

Jack and Karen turned to each other in bewilderment. " _Geeze_ ," Jack scoffed. "What's up his butt?"

"Not a man! Haha!"

Their loud, raucous laughter could be heard in all the surround apartments.


	3. Pt 3

Jack watched her pace back and forth in her closet from his spot on the chaise lounge. He makeup was flawless, hair curled in ringlets around her face, and the beautiful scent of her perfumed dabbed behind each ear. She had a black silk robe over her shoulders, untied and loose on her body. A lace thong covered her lower half, barely, and every time she moved about the room, grabbing skirts and blouses, Jack would catch a glimpse of her smooth, round breasts. He leaned back on his hands, his feet crossed in front of him as he sat on the edge of the chaise, a smile coming to his lips as Karen rambled about her clothes. It was nearly 10:30 and Karen promised Jack a day of shopping, but she had to make an appearance at work first.

She grabbed a pencil skirt and two blouses, one red, the other purple and walked them over to Jack, standing in front of him. "What do you think," she asked, holding the red up to herself with the skirt beneath. "Red," she switched the tops out quickly, "or blue?"

Jack frowned, annoyed that the clothes were covering her gorgeous body. He pretended to consider the items for a moment and then shrugged. "I dunno."

Karen sighed and threw the clothes to the floor, crossing her arms over her chest. "What's the point of having a gay best friend if you're not going to dress me?!" she shrieked at him, frustration written all over her face.

Jack smirked and sat up, planting his feet on the floor. He reached out and grabbed her by her arms, untangling them so he could press his face into her stomach and rest his hands on her hips. Karen subconsciously placed her hands on his shoulders and closed her eyes when Jack began to place kisses up her stomach and between her breasts. "That's not _all_ I'm good for, is it, Karebear?" he mumbled against her skin.

Karen bit her lip and looked down just as he moved one side of her robe off her shoulder revealing her breast. Her nipple hardened from the drafty air and she moaned, her eyes fluttering closed again when Jack latched his lips to the hardened bud. He began to suckle at her and she felt her knees go weak at the sensation. "I'm gonna be late for work," she attempted one last time. She felt him chuckle against her breast, the vibrations making her gasp.

He held a nipple between his teeth and looked up at her, but her eyes were closed tightly, her eyebrows knit together in pleasure. "You're already late for work." His words were muffled as he spoke, his mouth never parting from her and Karen groaned. He released her slowly, the suction making a pop sound as he moved back. He gave her little kisses along the curve of other breast that was still partially covered from the robe and he began to give her a hickey on the underside of it. He felt Karen's hand slide into his hair at the back of his head, guiding him to her neglected nipple and he smirked before capturing the rosy peak in his mouth.

She gasped, beginning to lose control of her breathing and dug her nails into his scalp, keeping him in place. Jack moved one of his hands from her hip down to between her legs, leaving a trail of fire along her skin. He pulled part of the material to the side and slipped his middle finger in, gathering the juices there, tracing her lips. Karen's knees buckled, but Jack's arm around her waist kept her from falling to the floor. Just when she thought he was going to press his finger right where she needed it most, he moved away from her, his mouth letting go of her nipple and his hand disappearing from her center. She opened her eyes to berate him, but then she felt him tugging her panties down her thighs. She steadied herself on his shoulders as she stepped out of them and watched him lay back on the soft cushion of the chaise. He reached up and dug his fingers into her hips pulling her to him until she was straddling his face. Karen's heart pounded in her chest rapidly in anticipation for what was about to happen. Jack only recently became curious about going down on her, but he had yet to actually do it. She braced herself by putting her hands on the back of the chair, wanting nothing more than to lower herself and ride his face until she exploded, but she restrained herself, knowing he wanted to figure out what drove her wild.

He lifted his head and licked her languidly, smirking when he felt her tremble against him. He had his arms hooked under her legs, his hands gripping her thighs to keep her legs spread for him. He pulled her further down and Karen put all of her weight into her legs, her feet planted on either side of the chaise. He ran his lips over her a few times, his tongue coming out to play. Her skin was silky smooth; she had just gotten a full Brazilian wax the day before, leaving no barriers between his lips and hers. She was whimpering above him, her hips bucking of their own accord and he took the hint. He slid his tongue inside of her, pumping it a few times teasingly before he brought his lips to her clit and then sucked hard.

Karen cried out, her eyes rolling back, and she breathed heavily. "Oh honey," she gasped, clenching her teeth in bliss. "Ungh, yes!"

Jack shoved his tongue back inside her and Karen began undulating her hips, her high pitched squeaks getting louder the closer she got to her orgasm. He slipped his tongue out and brought the muscle to her swollen clit, flicking it back and forth as she ground down on his face.

"Ah! I'm cumming!" she shrieked. "Yes, yes, ughhh! Ohh _fuck_!"

She drenched his chin and he moved his tongue back down to lick her cum, now addicted to the taste of her. He kept laving at her as she caught her breath, her thighs shaking beneath his hands. She reached her hand down and ran her fingers through his hair, delighting in the extra shots of pleasure that coursed through her until it became too much. She raised herself up on weak legs and Jack sat up, pulling her back down so she was straddling his hips. Karen grabbed his chin in her hand and brought her mouth to his, her tongue seeking his out so she could taste herself.

When she pulled away from him, Jack gave her a thoughtful look. She pouted at him, curious to where his mind was. "What, honey?"

Jack stared into her eyes, deep in thought until he finally spoke. "I think you should go with the purple top and the Chanel pumps."

Karen tossed her head back and let out a boisterous and contagious laugh.


	4. Pt 4

"Hey kids," Karen greeted as she entered Will and Grace's apartment.

"Hey, Kare!" Jack smiled, admiring the pep in his best friend's step. "You're pretty cheerful tonight. Score a few uppers?"

"Nah, honey," Karen waved him off, earning a side-look from Grace and a glare from Will. She gestured to her glowing face with a grin. "This is just after-glow of a great, mind blowing, orga-"

"Okay!" Will interrupted, clapping his hands together loudly. "Who's ready to eat?"

Karen and Jack shared a pout, but said nothing more as they sat down at the table along with Grace, who looked utterly confused by the whole situation. Will set the food on the table and the group began filling their plates quietly. Once the wine was poured, Grace took a sip and looked over at Jack who was digging into his chicken. "So Jack," she addressed the man across from her. "You must have been having some fun last night with a date." She raised her eyebrows suggestively and winked at him.

Jack gawked, unsure of what to say, but luckily Karen interjected, amusement crossing her face. "What do you mean, Gracie?"

"Well," Grace drew the word out, clicking her tongue against her teeth. "Will and I got back from the movies a little late last night and heard some not-so-discreet sounds coming from Jack's."

"Grace," Will started, but Jack interrupted him.

"Oh that!" Jack remembered the events of the evening and grinned cheerfully. "No, I didn't have a date over. Karen and I were-"

"Watching porn!" Will exclaimed causing all eyes to turn on him. "Yup. That's what they were doing."

Karen, realizing Will was trying to spare Grace from finding out about her and Jack's arrangement, rolled her eyes in exasperation. "For fucksake, Wilma, we were not watching porn!"

Grace's face was a mixture of complete confusion and regret, starting to hate that she even brought the subject up. "Then what were you-"

Jack rolled his eyes, chewing a piece of chicken loudly as he spoke. "Karen was giving me a titty-fuck, duh!"

"WHAT!"

The sound of utensils clattering against porcelain rang out throughout the apartment. Will dramatically stood from the table and stomped up to the kitchen, tossing his plate carelessly in the sink. Grace's eyes were bugged so far out of her head, Karen thought they were gonna fall out. They all just stared at each other, Jack and Karen clueless to what was wrong, Will looking pissed off, and Grace in a state of shock. The room was painted in a painfully uncomfortable silence. Karen sighed in annoyance, waiting for the barrage of questions she knew were going to be hurled their way.

"K-Karen..." Grace stuttered. "Was giving you a _what_?"

Jack swallowed his food and scrunched his face up in agitation. "A titty fuck," he repeated. "Ya know... She was on her back and I was on top of her with my dick between her-"

"I _know_ what a titty-fuck is!" Grace exclaimed, holding her hand out as if the gesture would bar him from continuing. Her eyes were shut tight, trying to rid herself of the image of Jack and Karen doing _anything_ sexual. "What the hell is going on?"

Will stepped down from the kitchen, his arms crossed over his chest. "These two have decided to form some sort of sickening "friends with benefits" relationship," he informed his friend, a look of disgust on his face.

Karen got fed up and threw her napkin on the table, standing in anger. "Oh _fuck off_ , Wilma," she sneered at him. "You don't have to get all pissy and judgmental just because you don't have someone to suck you off every night like Jack does. I'm sick and tired of your constant glaring and obnoxious comments that you've been tossing our way the past few weeks. Either grow a pair or stay out of our business!"

"Wait," Grace spoke up, looking at Will. "You knew?"

"He walked in on me fingering Karen in my kitchen a few weeks ago," Jack spoke up, taking another bite of his food.

"Jack, _please_ ," Grace pointed to him. "I do _not_ need details on what you were doing." Her gaze fell back on Will who was currently in a death glare match with Karen. "You knew this was happening and you didn't tell me?"

"It's non of your fucking business." Karen muttered angrily, her eyes still locked on Will.

"Yes, I knew it was happening," Will said with a sigh. "But how exactly did you expect me to tell you? ' _Hey, Gracie, how was work? Oh, did you know Jack and Karen are fucking? So what do you want for dinner'_?" he mocked with disdain.

"We're not _fucking_ ," Jack scrunched his face up. After a moment of hesitation, he added, "Not in the traditional sense anyway."

"I don't care _how_ you tell me, just that you tell me!" Grace exclaimed.

"What part of 'none of your business' do you two not understand?!" Karen shouted, silencing the entire group. "Jack and I have an agreement. We get each other off whenever we feel like it and that's it. I don't care if you think it's a bad idea or even what you think at all because our business and ours alone. Now, if you'll excuse me, I'm going home." She grabbed her coat and purse as she made her way to the door. "Jack, I'll see you tomorrow." The door slammed in her wake and they all jumped from the sound.

Will shook his head and turned his attention to Jack who began to stand from the table. "Jack," he said calmly, grabbing his friend's arm to stop him from leaving right away. "Don't you see she's manipulating you? Using you?"

"What are you talking about?" Jack looked confused, but Will saw the hints of anger beginning to form in his eyes.

"You're gay, Jack!" Will said, waving his arms at him. "And you're being sexual with a woman!"

"I'm being sexual with Karen," Jack glowered. "I've always been sexual with Karen. Why is this such a hard concept for you to grasp?"

"Because it's Karen!" Will screamed. "Because it's a woman! Because you're you!"

"Will," Grace tried, seeing the look on Jack's face, but it was too late. Jack was outraged.

"Listen to me, Will Truman," he began, his voice deep. "I love Karen. She is my best friend and has been for seven years. She and I have a bond that cannot and _will not_ be broken by you. I'm not attracted to women, I'm attracted to Karen because she gets me, she loves me for who I am, she supports me, and doesn't pretend to be anybody other than who she is. And she is fucking hot. Now either you accept that fact or you can fuck right off!"

With that he stormed out of the apartment, slamming the door behind him much like Karen did. He went right to the elevator, repeatedly hitting the 'down' button until the doors opened and he marched inside, on his way to the one place he knew he would be able to vent.

Inside, Will began angrily cleaning up dinner, tossing plates into the sink and slamming cabinets. Grace watched him for a minute until he broke a wine glass and then she intervened. "Will, why are you so pissed at them?"

'Because it's not right!" Will shouted, unable to control his emotions. "Because Jack was the one that made me come out and now he's off with a woman?"

"So what?" Grace countered. "When have Jack and Karen ever done anything normal?" She walked over to him, wrapping her arms around his shoulders. "Are you jealous?"

Will shrugged her off. "No, I'm not jealous. I guess I'm just... a little betrayed." He sighed, his eyes focused on the kitchen floor. "Jack I were the same and now..."

"Will," Grace wrapped her arms around his shoulders again and this time he didn't fend her off. "Jack and Karen are and always will be Jack and Karen. They've always had a sick, twisted relationship that we will never understand, but that's what makes them Jack and Karen." She shook her head, placing her chin on his shoulder. "And they're right," she sighed "We have no right to judge them or their relationship."

Will hated to admit it, but he agreed. "Yeah, I guess you're right," he acquiesced. "Damn, now I have to do the one thing I swore I'd never do in my life."

"What's that?"

"Apologize to Karen."

* * *

Jack arrived at the manse not too long after Karen. When he entered her bedroom, closing and locking the door behind him, he found Karen in the midst of undressing.

"Jack?" she asked, turning to face him from the sound of the door slamming. "What are you doing here?"

Jack didn't answer. Instead, his eyes took in the sight of her luscious curves that were on display before him as she stood in only her bra and panties, her skirt in a pool at her feet. He rushed over to her, tearing his shirt and pants off as he went. Karen stared at him wide-eyed, her surprise increasing when she saw his stiff erection bobbing between his legs. She no longer held the need to question him. Her panties were soaked in seconds. When he reached her, her grabbed her and she wrapped her legs around his waist, their mouths melding together instantaneously. He carried her until he hit the wall near the entryway to her closet. Karen held tightly to him, her arms wrapped around his neck and Jack moved his arms to her back, unhooking her bra and tossing it over his shoulder when her arms were freed from the straps. He reached between them with one hand, the other kneading her breast as she whimpered, and he hooked his fingers in the gusset of her panties, yanking it roughly. The thin material tore and Karen gasped as the now useless material fell to the ground.

Jack moved his hand to the back of her knee, unwrapping one leg from around him and he pushed it up so it was by Karen's head, repeating the motion with the other leg. Karen pulled away from their kiss and screamed out when Jack thrust inside of her fully. This was the first time ever that he was actually inside of her, his cock throbbing between her legs. He let her adjust to him for a few moments, ignoring the questions burning in her eyes, and then he began to thrust up, moaning as she gripped him. Karen dug her nails into his shoulders and she squeaked every time he filled her. It was like his cock was made for her, hitting that spot inside of her effortlessly. She reached a hand up, desperate to hold on to something. The only thing she found was a wall sconce above her head and she latched on, gripping it as hard as she could while Jack pumped into her fast and hard.

"Uh, fuck, yeah," he groaned, watching their coupling between their bodies. Karen began to pulsate around him and he knew she was about to cum. He looked up to see her eyes were closed in pleasure and he increased his speed. "Look at me, Karen," he demanded. "Look at me while I fuck you. Look. At. Me." Each word was emphasized with a harsh thrust of his hips and Karen screamed, her eyes opening just in time for her orgasm to sweep over. Jack came the second he felt her clenching down on him, his eyes once again locked on the sight of himself pushing his way inside of her. He finally pulled out, his cock still slightly hard as it bobbed up and brushed against her clit. Karen gasped and gently pushed at his shoulders. Jack eased her legs down, but she fell forward, pushing them both to the ground.

She rolled off of him and laid on her back, gasping for breath as air struggled to find it's way into her lungs. "Sorry," she said. "But I can't feel my legs."

He chuckled, his chest heaving. "Me neither."

When they finally settled down, Karen turned her head to stare at him. "We just had sex," she state obviously. "Like real sex."

"We did," Jack nodded, looking at her.

Karen narrowed her eyes and pursed her lips at him thoughtfully. "Is this because of Will?" she asked.

Jack raised his eyebrows. "What?! No!" Karen just stared at him. "Okay, part of it was, yeah," he confessed. "He pissed me off after you left, but I was only coming over here to vent. And then I saw you and... and I just had to have you."

Karen grinned gleefully at that. She rolled over and threw her leg over his midsection, her hands on either side of his head as she smirked deviously down at him. "Well, now you've had me, honey." She leaned down and captured his lips, but pulled away before he could respond. "And you're gonna have me again and again until I'm through with you."

He beamed. "Sounds like a plan."


	5. Pt 5

Karen casually limped through the doors of Grace Adler Designs and tossed her purse carelessly to the floor before slowly sitting down in the chair at her desk. She felt eyes on her the second she walked in, but she desperately tried to ignore them and began to fiddle idly with the various nail polishes and magazines in front of her. A shadow of a tall skinny woman came over her and she pursed her lips, keeping her attention on the Vogue magazine she just flipped open, pretending to be very interested in the pictures it displayed.

"Karen..."

She flinched at the sing-song way Grace said her name, but kept her eyes down. "What?"

"Oh come on!" Grace exclaimed, pulling her stool over and plopping it right down next to Karen's chair. "I wanna hear all about you and Jack!"

She sighed, flipping the page and tilting her head. "Listen, just cause I get to sleep with my gay best friend and you don't get to sleep with yours doesn't mean-"

"Oh give it up, Karen, you're dying to talk to someone. I can see it in your dilated pupils!"

"Grace-"

"Karen, you limped in here."

Karen bit her lip and gave Grace a quick side-glance. "I, uh, twisted my ankle when I was chasing Rosie with her hormone shots so she stays a woman! You know, they say after fifty-"

"I know you're lying. You weren't favoring one leg for the other, you were trying desperately to ignore that oh-so-good sore burn between your legs." She smiled deviously as a red blush began to creep up Karen's neck. "Spill, Karen! And don't leave anything out!"

Karen dropped the magazine and crossed her arms over her chest, acquiescing. "All right, all right, I'll talk. Just don't say anything to Wilma. That Queen is still on the top of my list and I don't want to give him more fuel to judge me and Jackie."

"I promise I won't say a word." Grace held up three fingers in the 'Girl Scout Honor'. "So is he good? Ya know, for a gay guy? I mean he has to be good, you can barely walk. But like how good?"

Karen rolled her eyes and sighed loudly, dropping her hands to her lap. "Are you gonna let me tell you or are you gonna keep talking, Ramblin' Ann?"

Grace held her hands up in an apology. "Okay sorry, sorry, you talk. You talk."

Karen eyed her as if waiting to see if Grace was going to blab again and when it seemed like she wasn't, Karen began to explain. "Well, he's kind of amazing, Gracie," she said with a grin. "He's caring, attentive, passionate-"

"Oh forget that crap!" Grace interrupted with a wave of her hand. "I said details!"

Karen huffed in frustration. "Like what?!"

"Like how often are you guys together? What does he do to you? How did it even start?" Her eyes were lit up and she was practically bouncing in her seat.

Karen frowned and sat back, thinking back to all those months ago when she and Jack first started this rendezvous. A slow grin came to her lips and she looked off into the distance as she remembered. "Well, we were at his place watching gay porn..."

* * *

 _The men on the screen were moaning and groaning obnoxiously and Karen shifted in her seat uncomfortably, her panties damp from her arousal. The movement caught Jack's eye and he turned to look at her. His eyes flickered back to the screen momentarily as the buff plumber gave the pool-boy a blowjob before he put his attention back on Karen with an inquisitive frown._

 _"Kare, are you any good at blowjobs?" he asked bluntly._

 _Karen's eyes widened and she slowly turned her head to stare at him. "What?"_

 _Jack raised his shoulders, gesturing towards the TV as he repeated himself. "Are you any good at blowjobs?"_

 _Karen raised her eyebrow and contemplated the question for a moment. She knew she was great at blowjobs, many men had told her so in the past. Hell, she was great at everything sex related. She pursed her lips and turned her body slightly toward him, an eyebrow raised suggestively. "Well, honey," she said seductively. "There's only one way to find out."_

 _Jack frowned, confused as to what she meant until he felt her hand caressing his thigh. He looked down at her hand as it inched daringly up towards his crotch and then back down again. "Uhhh, Karen? What are you doing?"_

 _She shrugged, but didn't stop her hand's movements. "If you wanna know if I'm good at blowjobs, I'll show you."_

 _Jack didn't know what to say, his mouth opening and closing every few seconds. He looked between the TV, Karen's mischievous eyes, and the hand that now lay perfectly on his crotch. "Okay."_

 _Karen was surprised, but she quickly recovered and licked her lips. She took her hand off him and reached for the TV remote, but he grabbed her wrist to stop her, silently telling her to leave it on. Karen smiled wryly and turned the set off, the room suddenly becoming dimmer. "You won't need it," she said, her voice husky. Jack audibly gulped, his eyes locked on Karen as she stood from the couch and moved to her knees in front of him. She parted his knees, her hands sliding up his jean covered thighs until she reached the button of his pants. She unbuttoned his jeans and pulled the zipper down slowly, already hearing Jack's breathing deepen above her. She pushed the material down and slipped her hand inside, finding his already hardening cock easily and pulling him out. Her hand loosely held him at the base, her eyes hungry at the sight of him. She looked up and locked her eyes on Jack's and then licked the underside of his cock from the base to the tip._

 _Jack groaned loudly and his head fell back against the couch. Karen smirked and swirled her tongue around the tip of him a few times before she wrapped her lips around him and slowly moved her head down. She felt the tip of him hit the back of her throat and she held him there for a bit before she lifted back up, her tongue tracing the vein on the underside of his cock. Jack let out another moan, his hands squeezed into fists on top of his thighs. Karen repeated the action a few more times, loving the taste and feel of him in her mouth. She kept her eyes on him, delighting in the pleasure on his face._

 _"Ohhh, shit," he gasped. He squeezed his eyes shut, ready to blow when Karen suddenly pulled away. His eyes popped open and he looked down, his chest heaving at the loss of his orgasm. "Karen!" he exclaimed in frustration. She winked at him and then took him in fully, sucking him as she moved up and down at a quick, steady pace. Jack took in a sharp breath and began breathing heavily again, biting his lip hard. He came a few seconds later, moaning as his cock twitched inside Karen's mouth. He slumped against the couch, getting his breathing under control when he felt himself slip out of her warm mouth. He opened his eyes and saw Karen tucking him back into his pants. She raised herself off the floor and moved to sit on his lap, her legs tossed to the side of him and her arm around his neck, a hand on his chest above his fast beating heart._

 _Karen licked her lips and beamed at him. "So?" she asked._

 _Jack finally caught his breath and patted her thigh with a nod. "Yup," he said. "You're definitely good at blowjobs."_

* * *

"...And then it progressed from there," Karen shrugged. "A few months later he started getting me off instead of me getting myself off and then a few days ago we-" She stopped suddenly, unsure if she should reveal that they finally had full on sex. She didn't care about telling her friend, but she wasn't sure if Jack would mind.

"A few days ago...?" Grace asked, waving her hand in front of her to provoke Karen to continue. Then it dawned on her and she gasped in rapid succession. "You had sex with him!"

Karen rolled her eyes. "Yes," she sighed. "We finally had sex the other night after dinner at your apartment."

"This is so crazy," Grace shook her head, but the smile stayed on her face. "So, why are you really limping?"

Karen grinned wickedly as the memories of the night before and this morning flooded her mind. "Well, since we discovered how even more amazing it is to be together in _every_ way, we spent most of the night trying different positions." She leaned forward and laid a hand on Grace's on her desk. "Oh honey," she breathed out. "The things that boy can do to me. At one point he had me bent over and was fucking me so hard that I came three times in a row."

Grace raised a hand and began fanning herself. "Damn, that's hot."

"Mhm," Karen nodded, sitting back in her chair. "I've never been more sexually satisfied in my life. I mean, before Jack, I've only been able to squirt when I was by myself-"

"Ooookay," Grace interrupted as she stood, walking back to her desk. "I think that's too many details."

Karen squinted her eyes at the redhead, picking her magazine back up. "Whatever. You're just mad because you can't do it."

Grace scoffed. "How do you know I can't squirt?" Karen didn't answer and Grace suddenly became very self-conscious, glancing every few seconds at Karen's prideful look. "Anyway, I think it's nice that you and Jack are able to do all that crazy stuff and stay good friends."

"Yeah," Karen smiled fondly, thinking about her Poodle. Her thoughts almost too quickly became dirty and she shifted in her chair, clearing her throat. "Enough of me and Jack though, don't you have to find some place for homeless people to live or whatever the hell you do with people and furniture?"

Grace stared incredulously at her before scoffing again. "I'm an interior designer, you boozed up space cadet," she muttered under her breath as she began coloring her sketch.

"Did you say something, honey?"

"Nope."


	6. Pt 6

Karen sat on the stool in front of the vanity mirror in her room at the country club at Shelter Island, pinning her curled hair up and out of her eyes, leaving a few ringlets down to frame her face. The Valentine's Dance ended about an hour ago, Scott Wooley long gone, and the 'no homos allowed' fiasco done and over with. She was looking forward to this evening all week, excited to meet her date only to be utterly disappointed and left wanting when it didn't work out. She moaned in frustration and ground her hips into the chair, feeling her arousal coat her panties. She spread her legs and moved her hips back and forth a bit, stimulating her clit and biting her lip, but it wasn't nearly enough. She sighed and stood up to slide her panties down her legs before she grabbed her room key and exited the suite. She padded down the hall and paused in front of the door, praying she remembered their room assignments correctly and knocked lightly. She heard some movement on the other side and then the latch unlock, the door opening to reveal her best friend.

He had just gotten out of the shower, his hair still wet. He wore only a pair of loose sweatpants that he seemed to just toss on before opening the door. His strong, muscular chest glistened slightly with water droplets and she could see the beginnings of his happy trail from the low slung waistband of his pants. She raised her eyebrow at him, biting her lip seductively as she appraised his sumptuousness.

Jack knew what she wanted the second he saw her standing there in her pink silk nightgown. He could clearly see the lust in her eyes and he felt his cock twitch slightly, the tip poking the material of his pants. Her eyes were immediately drawn to the movement and she took it as a sign to enter the room, her hand pushing against his chest to move him back and then she shut the door with her foot. She backed him up until they reached the middle of the room, the soft bear skin rug tickling their toes and the warm comforting heat from the roaring fire caressing their legs. She trailed her finger from his chest down to his abs and then to the waist band of his pants, hooking her finger in and pulling it slightly and then letting go so it snapped against him. Their eyes stayed locked, her head tilted up and his looking down, their height difference almost comical. It was unspoken when she asked him to kiss her. He leaned his face towards her and placed a subtle kiss upon her waiting lips. He moved his arms to wrap around her waist, but she swatted him away, deepening the kiss by flicking her tongue out to tease against his lips. He put his arms back to his sides and Karen traced her fingers over the waist band of his pants around to his backside. Her fingers dipped under the material, pushing it down until it was resting under his butt cheeks and then she grabbed his ass, squeezing and massaging. Jack moaned into her mouth, feeling his cock brushing her stomach and he involuntarily thrust his hips up, the friction driving him wild.

Karen pushed his pants the rest of the way down so they were in a heap around his ankles and he reached out to touch her again, but she slapped his hands away once more. He growled and parted their lips, his mouth opening to chide her, but she pressed a finger to his lips to silence him before before he could speak. She grabbed his hips and began to sink to the ground, instructing him to follow her. She pushed him back on to the white bear skin rug and crawled over him, her thighs on either side of his hips. She placed open mouthed kisses on his chest, her nails gently scraping across his chiseled abdomen, moving down until they tangled in the trail of hair before moving back up again. He whimpered and she felt his cock twitch beneath her again, a smile breaking out over her lips. She dragged her tongue down his body and then opened her mouth to take his erect member in, sucking gently at the head. His thighs stiffened and he grasped at the rug, restraining himself from touching her like he so desperately wanted to. She relaxed her throat and opened her mouth wide and began bobbing her head up and down, moaning when she felt her own arousal begin to drip from between her legs. She used only her mouth to pleasure him, her hands caressing his thighs and hips.

Jack squeezed his eyes shut and groaned loudly, signaling that he was near the edge, so Karen released him from her mouth. He breathed heavily and fluttered his eyes open, seeing Karen grinning devilishly as she moved up his body. She sat on his chest and he felt her arousal drip into him, his nostrils filling with her womanly scent, making him dizzy with desire. She leaned down and captured his lips between hers and then shifted her hips down until she felt the tip of him bump against her clit. They shared a moan as their tongues tangled and Jack couldn't take it any longer; he raised his arms and planted his hands on her hips, digging his fingers into her flesh as he thrust up, entering her. They each gasped, their breaths mingling and then Karen sat up and began moving, rotating her hips slowly in a circular motion, her hands pressing against his chest to keep her balance. Her eyelids were hooded as she stared down into his blue orbs, her movements slow, but passionate. Jack tugged at the hem of her nightgown and Karen stopped moving for a moment, straightening up fully so she could pull the nightgown over her head, revealing her gorgeous body to him. She laid herself over him, her breasts against his chest, resting her forearms next to his head on the rug and she kissed him sensually. He began to thrust his hips up as she ground down on him, their pace quickening as they neared their releases.

They came together, breathy sighs escaping their lips. She bit his top lip as she came down from her high, slowing the movement of her hips and Jack tapped his tongue out against her bottom lip, their mouths melding together once more. They continued to share long, heavy kisses for a while, only parting when Karen began to lose feeling in her legs. She lifted up so he could slide out of her and then laid over him, her legs between his, her breasts pressed into his stomach and her ear resting on his chest, listening to his rapid heart beat as it slowed back down. Jack glided his hands down her smooth skin, resting his palms on her lower back and they watched as the fire began to dim, their eyes growing heavy and finally closing when it died out.


End file.
